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Janice White
Century 21 Carioti

Fine Homes & Estates
720 Celebration Ave., Ste 100

Celebration, FL 34747

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Homes for Sale in Winter Park, FL

Winter Park is a suburban city in Orange County, Florida, United States. The city was founded as a resort community mainly by northern business leaders in the late 19th and early 20th centuries. In the 1860s, Winter Park became the first planned community in Central Florida, strategically built around the railroad which served commerce and travel.  Winter Park’s main street includes civic buildings, retail, art galleries, a private liberal arts college, museums, a park, a train station, a golf course and country club, a historic cemetery, and a beach and boat launch. Mediterranean, Greek, Victorian, Revival, and Arts and Crafts period architecture create an eclectic atmosphere with many of the structures being more than 100 years old.

Known as the 'City of Gracious Living,' Winter Park, Florida, is one of America's most appealing cities. Its scenic beauty, tranquil environment, and abundance of art and culture have made it a showplace residential area since the late 1800's. The city is home to Rollins College, Full Sail University and the Charles Hosmer Morse Museum of American Art, which houses the largest collection of Tiffany glass. Winter Park features open park space, residential areas, and a street-side shopping district along Park Avenue where visitors can experience Winter Park’s charm with outdoor cafés, bistros and upscale specialty shops and boutiques.  The area is host to frequent art and music festivals. And, although it feels as if it's worlds away, it's only a few miles from downtown Orlando.



The population was 27,852 at the 2010 census. Winter Park is part of the Orlando–Kissimmee Metropolitan Statistical Area. 


Winter Park Neighborhoods

The scenic Olde Winter Park area is accented by small brick-lined streets that meander through quaint neighborhoods graced with old majestic oak and camphor trees forming a canopy draped with Spanish Mosss along the streetscape.  Picturesque lakes with old Venetian canals surround residential areas.  Beautiful parks, old majestic trees, and botanical gardens are abundant. Providing active and passive green space for residents and visitors is a priority for Winter Park city planners and helps maintain the charm that Winter Park has to offer.

Hannibal Square is what is called a legacy community.  Hannibal Square—the “west side”—was officially founded in 1881, only 40 years after Florida became the 27th state, and 14 years after the state reentered the Union.

From its' beginnings, Hannibal Square was rooted in faith, family and community. The west side was characterized by high levels of education, business and home ownership, and professional standing among its' African American residents.

For over one hundred years, the intersection of New England and Pennsylvania Avenues was the heart of the shopping and entertainment district for the local African American community.  Today's Hannibal Square merchants enjoy the neighborhood feeling that comes from being part of an existing community of residences, churches, community centers, playgrounds, train access and beautiful parks.

Although time has changed the character of the neighborhood, the merchants work hard to preserve the village ambiance, and to celebrate and support what is remaining of the historic neighborhood.


Park Grove was established in the late 1950's. The first houses were built in 1960. Park Grove can be identified by its pink subdivision wall, a small park located near the entrance at Park Avenue and Summerland Avenue and the oak-lined streets.

The homeowners association was developed in the mid -1960's when addressing issues fell upon the residents. The Board hosts an annual block party each year. Some of the activities at the block party have included street parties, barbecue dinners, chalk art on the streets, decorated bike competition, parades, children's theater group, Halloween parties and caroling and luminaries at Christmas.

The land on which Northwood Circle is located was formerly owned by Callie Colston Green whose desire was to see a subdivision developed for blacks.  Her desire became a reality when she teamed with the Sulphur Investment Corporation and H & M Construction Company of Winter Park to make it happen.

What makes this community unique and historical are the circumstances that brought about its development at that time.  Northwood Circle was the first and only subdivision in Winter Park that was conceived by blacks and developed for blacks; buying homes and living in other subdivisions in Winter Park at that time were not accessible to blacks. 

Orwin Manor remains one of the more desirable areas to live and has been cited as one of the fastest appreciating neighborhoods in the Orlando area. To insure that the neighborhood maintains its quality of life, a number of Orlando and Winter Park residential ordinances are strictly enforced.   You will find that once again, many young couples are raising their families in Orwin Manor. Its’ convenient location, variety of architecture, historic homes, mature street lined tree canopies make Orwin Manor a wonderful place to live.

The first homes in Orwin Manor’s Westminster Section were built starting in 1925. These homes were Mediterranean themed styles which virtually defined Florida's great 1920’s land boom era along with a variety of styles including colonial revival, mission, and bungalow. The streets of Orwin Manor, were lined with curbs, sidewalks, streetlights with underground wiring, oak trees and palms. When the land boom went bust, construction in Orwin Manor slowed and did not pick up again until the post WWII building boom when many vacant lots were cleared for new homes. Few of these used the Mediterranean themed styles from the previous decades.

Sevilla began its development in 1970. The land now contains 63 lots. Most of the homes were built in the early 1970’s, however, two homes have been built since 1995. The homes were built by prominent builders of the day including Charles Clayton who lived in Sevilla with his family for many years. Many of the original owners still reside in the community.

The community of Sevilla is located just off Pennsylvania Avenue in the heart of Winter Park; minutes away from Rollins College and the Park Avenue Shopping District. The community is bordered by Fawsett Road, Lake Sue and Mead Botanical Gardens. There is one entrance to the community on Pennsylvania Avenue.

Situated along the shores of three sparkling lakes, Windsong is a 200 acre community located in the center of Olde Winter Park and mirrors the old-world charm of the area. Windsong’s neighborhoods were developed around the Windsong estate which was built in 1904 by a Chicago industrialist.



Winter Park is home to the second oldest golf club in Central Florida.  The course makes its way through the downtown Winter Park area with its narrow, tree-lined fairways and postage stamp, bunker guarded greens and provides a challenge for beginning to expert golfers.

Winter Park offers a wide selection of festivals throughout the year to satisfy everyone's interests and the city draws thousands of visitors to its’ annual festivals including the Bach Festival, the nationally ranked Sidewalk Art Festival, and the Winter Park Concours d'Elegance. 

The Winter Park Sidewalk Art Festival is one of the nation's oldest and largest juried outdoor art festivals, rated among the top shows by Sunshine Artist and American Style magazines. In 2012, about 1,200 artists from around the world applied for entry, and an independent panel of judges selected 225 national and international artists to attend the show. The National Endowment for the Arts, the White House, Congress, and many others have honored the Festival for promoting art and art education in Central Florida. An all-volunteer board of directors runs the annual festival, now in its 50th year.

424 Results Days on Site (new to old)
$1,150,000 New For Sale
1098 McKean Circle
Winter Park, FL 32789
4 beds, 3 baths | Single Family Home
2,710 sq ft; lot: 20909 sq ft lot
$760,000 New For Sale
863 Granville Drive
Winter Park, FL 32789
4 beds, 2.5 baths | Single Family Home
2,305 sq ft; lot: 13939 sq ft lot
$649,900 New For Sale
5 beds, 3 baths | Single Family Home
2,647 sq ft; lot: 9148 sq ft lot
$224,900 New For Sale
5030 N Woodcrest Dr
Winter Park, FL 32792
4 beds, 1.5 baths | Single Family Home
1,141 sq ft; lot: 7841 sq ft lot
$275,000 New For Sale
7234 Knottypine Avenue #2
Winter Park, FL 32792
3 beds, 2 baths | Single Family Home
2,014 sq ft; lot: 16117 sq ft lot
$334,900 New For Sale
1630 Chestnut Avenue
Winter Park, FL 32789
2 beds, 2 baths | Single Family Home
1,622 sq ft; lot: 6534 sq ft lot
$5,500,000 New For Sale
1731 Pinetree Road
Winter Park, FL 32789
6 beds, 7.5 baths | Single Family Home
7,654 sq ft; lot: 0.68 acres
$895,000 New For Sale
1205 Whitesell Drive
Winter Park, FL 32789
4 beds, 2.5 baths | Single Family Home
2,897 sq ft; lot: 14810 sq ft lot
$1,140,000 New For Sale
1807 Via Amalfi
Winter Park, FL 32789
5 beds, 2.5 baths | Single Family Home
2,904 sq ft; lot: 0.53 acres
$454,990 New For Sale
1451 Lake Florence Way
Winter Park, FL 32792
3 beds, 2 baths | Single Family Home
2,189 sq ft; lot: 6098 sq ft lot
$139,995 New For Sale
270 Scottsdale Square #270
Winter Park, FL 32792
3 beds, 2 baths | Condo
1,300 sq ft; lot: 8712 sq ft lot
$220,000 New For Sale
700 Melrose Avenue #G 3
Winter Park, FL 32789
2 beds, 2 baths | Condo
1,074 sq ft; lot: 4356 sq ft lot
$179,000 New For Sale
5460 Bracken Court
Winter Park, FL 32792
2 beds, 2.5 baths | Townhouse
1,200 sq ft; lot: 6534 sq ft lot
$263,000 New For Sale
1825 Willow Ln
Winter Park, FL 32792
3 beds, 2 baths | Single Family Home
1,380 sq ft; lot: 9148 sq ft lot
$1,149,000 New For Sale
1210 Oaks Boulevard
Winter Park, FL 32789
3 beds, 3.5 baths | Single Family Home
2,680 sq ft; lot: 7405 sq ft lot
$1,179,000 New For Sale
615 N Phelps Avenue
Winter Park, FL 32789
4 beds, 4.5 baths | Single Family Home
3,009 sq ft; lot: 8276 sq ft lot
$460,094 New For Sale
2074 Laurelwood Way
Winter Park, FL 32792
4 beds, 3 baths | Single Family Home
2,185 sq ft; lot: 5663 sq ft lot
$551,315 New For Sale
1105 Wading Waters Circle
Winter Park, FL 32792
4 beds, 3 baths | Single Family Home
2,702 sq ft; lot: 8276 sq ft lot
$714,533 New For Sale
2181 Green Glade Loop
Winter Park, FL 32792
5 beds, 4.5 baths | Single Family Home
4,268 sq ft; lot: 13939 sq ft lot
$87,500 New For Sale
152 Lewfield Cir #152
Winter Park, FL 32792
1 bed, 1 bath | Condo
678 sq ft; lot: 151 acres
Listings 1-20 out of 424 Previous 1 2 3 4 5 Next
Janice White, Realtor®

720 Celebration Ave, Ste. 100
Celebration, FL 34747
Phone: 407-973-8762


Janice is first class. We purchased this property through her, unseen until we had near completion. That is how much we trusted her. We would never do that in the UK. Therefore when we reluctantly decided to sell there was no other choice of realtor. From the initial discussions with Jan to completion this sale has been painless. We trusted Jan to find us the right buyer for the right price and she did. We had a tenant in the property who Jan worked with to secure viewings. Her easy going, pleasant manner makes her a wonderful person to work with. She knows her market and gives good advice but is never pushy. Ian and I cannot praise her too highly. We feel very lucky to have come across Jan when we tentatively entered the Century 21 offices seven years ago. Janice White is the best! We need her in the UK! Ian and Jan Tyler
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